As loyalty programs look toward 2026, few categories are under more pressure to evolve than travel. Shifting consumer expectations, accelerating AI adoption, and rising demands for immediacy are forcing brands to rethink how loyalty shows up, not just at booking, but throughout the entire journey.
In this Supplier Voices conversation, Nowell Outlaw, Chief Executive Officer of Switchfly, shares how AI-driven planning, real-time relevance, and emotional engagement are reshaping what effective travel loyalty looks like, and where many programs still struggle to keep pace.
AI Moves From Concept to Expectation
For much of the past two years, AI dominated loyalty conversations without materially changing execution. That dynamic is now shifting.
“The elephant in the room is AI,” said Outlaw. “18 to 24 months ago, people really hadn’t embraced it. They didn’t fully understand it. Now it’s becoming very real, and people are starting to understand what those technologies can do, and how that’s going to change their programs.”
In travel, those changes are already being driven by consumers. Many travelers now begin planning with large language models, assembling itineraries before interacting with any brand-owned platform.
“There’s a disconnect,” said Outlaw. “I’ve planned my trip using a tool like ChatGPT. I know where I want to go, where I want to stay, what I want to do. What people don’t want is to take that list and then go into another system and try to book everything separately.”
From One-Stop Shopping to Dynamic Itineraries
That disconnect is pushing travel loyalty toward a more flexible, modular model -- one Outlaw describes as “choose your own adventure.”
“Travel is really becoming more of a choose-your-own-adventure experience. Large language model technology helps the consumer figure out what they want that adventure to be. But the ecosystem hasn’t fully caught up to that yet,” he said.
While one-stop shopping has long been a consumer goal, the modern version demands far more personalization, speed, and optionality. Loyalty programs that still operate around static earn-and-burn mechanics risk falling out of step with how people actually plan travel today.
Time-to-Value Becomes Non-Negotiable
As expectations shift, time-to-value has emerged as a defining loyalty challenge, especially in travel, where relevance is highly situational.
“It’s give to get,” Outlaw said. “How can I recommend things that are timely and reward someone while they’re actually on their journey?”
That might mean recognizing when a customer is mid-trip and offering value that aligns with their immediate context, rather than waiting until after the experience is over.
“If I know you’re on your way to Whistler and you just took an eight-hour flight, maybe I can offer you a massage at a discount when you get to your hotel. Those kinds of things matter in the moment,” he said.
Hyper-Relevance Without Crossing the Line
Real-time personalization introduces new risks alongside new opportunities. While travelers want relevance, they are increasingly sensitive to how much brands appear to know about them.
“There’s a fine line. You don’t want to be generic, but you also don’t want to be so hyper-personalized that people say, ‘This is a little eerie. It knows too much about me,’” Outlaw said.
Striking that balance will be critical as AI becomes more embedded in loyalty execution. Programs that misuse personalization risk eroding trust rather than deepening engagement.
Why Travel Creates Emotional Loyalty
Among all redemption categories, travel occupies a uniquely emotional space, one that Outlaw believes brands often underestimate.
“You don’t necessarily get emotional loyalty by redeeming for a gift card or a blender,” he said. “Travel has an emotional attachment that other rewards just don’t.”
The value of travel rewards extends well beyond the trip itself. Experiences become stories, memories, and social currency, shared long after the points are redeemed.
“You don’t come back from a trip and talk about what you got for Christmas. You talk about where you went, what you learned, and you show pictures. That emotional layer just doesn’t exist with merchandise,” Outlaw said.
AI Readiness Remains Uneven
Despite rising interest, AI maturity varies widely across organizations. Larger brands might have dedicated teams and infrastructure, while smaller programs rely on existing tools layered onto legacy systems.
“There are a lot of people who think they’re AI experts because they’ve been using ChatGPT for six months,” Outlaw said. “Real AI expertise takes years. The people who truly understand it are busy…and expensive.”
That reality makes strategic decision-making even more critical. In a fast-moving landscape, brands must choose technologies carefully, knowing that today’s decision may need revisiting within months.
“The hardest thing for brands is figuring out where to place their bets. Once you standardize on a tech approach, it takes time to roll out and support. You need the right people to help you make those choices,” Outlaw said.
Re-Energizing Dormant Loyalty
Outlaw is particularly optimistic about AI’s ability to re-engage members with large, unused point balances.
“There are so many people with massive point balances who never spend them,” he said. “Not because they don’t value the program, but because they’re not finding what they want.”
Smarter personalization, better recommendations, and more relevant redemption options could help close that gap, turning passive members back into active participants.
As loyalty programs head into 2026, the challenge is no longer whether AI will matter. The real question is whether brands can use it thoughtfully, connecting intent to action, relevance to emotion, and technology to genuine loyalty.